For the November 2008 issue of ISLANDS, research editor Ashley Knaus uncovered these top picks for island trips you can start planning right now. See which trip sounds best to you. And for another great idea, ISLANDS editor-in-chief Eddy Patricelli just returned from Grenada's LaSource resort, which is extending its summer rates through December, starting at $225 per night, per person. (To read about his LaSource trip, click here.)

Porto Santo, Portugal

Why Here - Weather. Unlike beachless big sister, Madeira, tiny Porto Santo is a beach lover's dream -- even in the winter. Think year-round temps in the 70s, six miles of light-yellow sand said to be rich in magnetic healing properties, and European cafés just a few feet from warm Atlantic waters. Stroll farther from the beaches to see sand give way to fields of grapes for authentic island wine.

When to Go - New Year's. Avoid crowds (and cold weather back home) and travel to Porto Santo at the end of December into early January. This island getaway might seem complicated planning-wise, but with travel specials and provided itineraries, the Portuguese tourism board suggests booking only one or two months in advance.

What to Budget - $3,500 (six nights, two people). Azores Express, part of the SATA Group, offers packages starting at $1,169 per person to the Madeira islands, including hotel there and airfare from Boston's Logan International Airport (BOS). Choose between high-end properties with seaside views and saltwater pools. Your budget should factor in transfers, food and activities. sata.pt

Maui, Hawaii

Why Here - Whale watching. After a summer feeding in Alaska's cool waters, North Pacific humpback whales migrate to the consistently warm Hawaiian waters for breeding season -- and most go to Maui. The whales are attracted to Maui's shallow south and western coasts, and -- lucky for viewers -- the whales like to come very close to shore. Hawaii is the only U.S. state where these whales choose to mate, calve and nurse their young, so be on the lookout for mothers breaching alongside their cute calves. They surface about every 15 minutes to breathe, so you won't have to wait long.

When to Go - February. Summer starts peak (expensive) season. So combine prime whale-watching season (December to May) with low season and mild temperatures.

What to Budget - $4,000 (five nights, two people). You don't have to join a whale watching tour to see these huge creatures. Beaches in Kapalua and the Makena Beach State Park have regular sightings. But to get on the water and be one with the whales, join Pacific Whale Foundation's Eco Adventures. Two-hour cruises with an expert on a catamaran start at around $30. Airfare from Los Angeles (LAX) to Kahului (OGG) runs around $800. Stay at the Ritz-Carlton, Kapalua or at the Grand Wailea Resort Hotel & Spa. Rates from $550. pacificwhale.org

Puerto Rico

Why Here - Good deals; direct flights. While airfare to other Caribbean islands has gone up, Puerto Rico remains dramatically lower than its counterparts.

When to Go - March. Peak season is December to May, but the west side of the island remains very quiet. Get the best of both worlds. Enjoy all the festivals that high season brings, but escape to the Cabo Rojo area, which offers some of the world's best beaches, including Boqueron Bay Beach.

What to Budget - $1,500 (five nights, two people). Flights from Miami (MIA) to San Juan (SJU) hover around $300, and when booked in advance, hotels can stay under $150. gotopuertorico.com